Catalysts and methods for ring opening metathesis polymerization

Schrock, Richard Royce; Autenrieth, Benjamin

Title: Catalysts and methods for ring opening metathesis polymerization

Patent · Tue Apr 03 00:00:00 EDT 2018

OSTI ID:1433368

Schrock, Richard Royce; Autenrieth, Benjamin

The present invention, among other things, provides highly syndiotactic poly(dicyclopentadiene) and/or hydrogenated poly(dicyclopentadiene), compositions thereof, and compounds and methods for preparing the same. In some embodiments, a provided compound is a compound of formula I, II or III. In some embodiments, a provided method comprises providing a compound of formula I, II or III.

View Patent

Cite

Export

Save

Research Organization:: Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-86ER13564

Assignee:: Massachusetts Institute of Technology (Cambridge, MA)

Patent Number(s):: 9,932,440

Application Number:: 15/452,505

OSTI ID:: 1433368

Resource Relation:: Patent File Date: 2017 Mar 07

Country of Publication:: United States

Language:: English

References (33)

Dicyclopentadiene polymer containing elastomer Klosiewicz, Daniel William https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/4657981 US Patent Document 4,657,981	patent	April 1987
Tungsten oxo alkylidene complexes for Z selective olefin metathesis Schrock, Richard R.; Peryshkov, Dmitry Vyacheslavovich; Hoveyda, Amir H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/9085595 US Patent Document 9,085,595	patent	July 2015
Tungsten OXO Alkylidene Complexes for Z Selective Olefin Metathesis Schrock, Richard Royce; Peryshkov, Dmitry Vyacheslavovich; Hoveyda, Amir H. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20130116434 US Patent Application 13/671109; 20130116434	patent-application	May 2013
Synthesis of Highly Cis, Syndiotactic Polymers via Ring-Opening Metathesis Polymerization Using Ruthenium Metathesis Catalysts Rosebrugh, Lauren E.; Marx, Vanessa M.; Keitz, Benjamin K. Journal of the American Chemical Society, Vol. 135, Issue 27, p. 10032-10035 https://doi.org/10.1021/ja405559y	journal	June 2013
Syndioselective Ring-Opening Metathesis Polymerization of endo-Dicyclopentadiene with Tungsten Complexes Having Imido Ligands: Development of Crystalline Syndiotactic Hydrogenated Poly(endo-dicyclopentadiene) Hayano, Shigetaka; Tsunogae, Yasuo Macromolecules, Vol. 39, Issue 1, p. 30-38 https://doi.org/10.1021/ma052088c	journal	December 2005
The polymerization of dicyclopentadiene: an investigation of mechanism Davidson, T. A.; Wagener, K. B. Journal of Molecular Catalysis A: Chemical, Vol. 133, Issue 1-2, p. 67-74 https://doi.org/10.1016/S1381-1169(98)00091-0	journal	July 1998
Five-Coordinate Rearrangements of Metallacyclobutane Intermediates during Ring-Opening Metathesis Polymerization of 2,3-Dicarboalkoxynorbornenes by Molybdenum and Tungsten Monoalkoxide Pyrrolide Initiators Flook, Margaret M.; Börner, Janna; Kilyanek, Stefan M. Organometallics, Vol. 31, Issue 17, p. 6231-6243 https://doi.org/10.1021/om300530p	journal	August 2012
Synthesis of cis,syndiotactic ROMP Polymers Containing Alternating Enantiomers Flook, Margaret M.; Ng, Victor W. L.; Schrock, Richard R. Journal of the American Chemical Society, Vol. 133, Issue 6, p. 1784-1786 https://doi.org/10.1021/ja110949f	journal	January 2011
Z-Selective and Syndioselective Ring-Opening Metathesis Polymerization (ROMP) Initiated by Monoaryloxidepyrrolide (MAP) Catalysts Flook, Margaret M.; Gerber, Laura C. H.; Debelouchina, Galia T. Macromolecules, Vol. 43, Issue 18, p. 7515-7522 https://doi.org/10.1021/ma101375v	journal	September 2010
Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide Complex Flook, Margaret M.; Jiang, Annie J.; Schrock, Richard R. Journal of the American Chemical Society, Vol. 131, Issue 23, p. 7962-7963 https://doi.org/10.1021/ja902738u	journal	June 2009
Ring-opening polymerization of endo and exo-dicyclopentadiene and their 7,8-dihydro derivatives Hamilton, James G.; Ivin, Kenneth J.; Rooney, John J. Journal of Molecular Catalysis, Vol. 36, Issue 1-2, p. 115-125 https://doi.org/10.1016/0304-5102(86)85107-0	journal	July 1986
A New Method for Catalytic Syntheses of Block Copolymers via ROMP: Development of Stereoblock Copoly(endo-dicyclopentadiene) Hayano, Shigetaka; Tsunogae, Yasuo Chemistry Letters, Vol. 37, Issue 5, p. 518-519 https://doi.org/10.1246/cl.2008.518	journal	May 2008
Hydrogenated Ring-Opened Poly(endo-dicyclopentadiene)s Made via Stereoselective ROMP Catalyzed by Tungsten Complexes: Crystalline Tactic Polymers and Amorphous Atactic Polymer Hayano, Shigetaka; Takeyama, Yoshihisa; Tsunogae, Yasuo Macromolecules, Vol. 39, Issue 14, p. 4663-4670 https://doi.org/10.1021/ma0604340	journal	June 2006
Iso- and Syndio-Selective ROMP of Norbornene and Tetracyclododecene: Effects of Tacticity Control on the Hydrogenated Ring-Opened Poly(cycloolefin)s Hayano, Shigetaka; Nakama, Yuki Macromolecules, Vol. 47, Issue 22, p. 7797-7811 https://doi.org/10.1021/ma502020u	journal	November 2014
Stereospecific Ring-Opening Metathesis Polymerization of Cycloolefins Using Novel Molybdenum and Tungsten Complexes Having Biphenolate Ligands. Development of Crystalline Hydrogenated Poly(endo-dicyclopentadiene) and Poly(norbornene) Hayano, Shigetaka; Kurakata, Hiroshi; Tsunogae, Yasuo Macromolecules, Vol. 36, Issue 20, p. 7422-7431 https://doi.org/10.1021/ma034611y	journal	October 2003
Stereospecific Ring-Opening Metathesis Polymerization of endo-Dicyclopentadiene by Schrock–Hoveyda Catalyst and Novel Mo- and W-based Complexes. Development of Crystalline Hydrogenated Poly(endo-dicyclopentadiene) Hayano, Shigetaka; Kurakata, Hiroshi; Uchida, Daisuke Chemistry Letters, Vol. 32, Issue 8, p. 670-671 https://doi.org/10.1246/cl.2003.670	journal	August 2003
Syndiospecific Ring-opening Metathesis Polymerization of endo-Dicyclopentadiene by Tungsten(VI) Phenylimido Catalyst Hayano, Shigetaka; Tsunogae, Yasuo Chemistry Letters, Vol. 34, Issue 11, p. 1520-1521 https://doi.org/10.1246/cl.2005.1520	journal	November 2005
Syntheses of Tungsten tert-Butylimido and Adamantylimido Alkylidene Complexes Employing Pyridinium Chloride As the Acid Jeong, Hyangsoo; Axtell, Jonathan C.; Török, Bela Organometallics, Vol. 31, Issue 18, p. 6522-6525 https://doi.org/10.1021/om300799q	journal	August 2012
Z-Selective Ring-Opening Metathesis Polymerization of 3-Substituted Cyclooctenes by Monoaryloxide Pyrrolide Imido Alkylidene (MAP) Catalysts of Molybdenum and Tungsten Jeong, Hyangsoo; Kozera, Daniel J.; Schrock, Richard R. Organometallics, Vol. 32, Issue 17, p. 4843-4850 https://doi.org/10.1021/om400583t	journal	August 2013
Cis-Selective Ring-Opening Metathesis Polymerization with Ruthenium Catalysts Keitz, Benjamin K.; Fedorov, Alexey; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 134, Issue 4, p. 2040-2043 https://doi.org/10.1021/ja211676y	journal	January 2012
Regio- and Stereoselective Ring-Opening Metathesis Polymerization of 3-Substituted Cyclooctenes Kobayashi, Shingo; Pitet, Louis M.; Hillmyer, Marc A. Journal of the American Chemical Society, Vol. 133, Issue 15, p. 5794-5797 https://doi.org/10.1021/ja201644v	journal	March 2011
Acyclic metathesis polymerization: the olefin metathesis reaction of 1,5-hexadiene and 1,9-decadiene Lindmark-Hamberg, Monica; Wagener, K. B. Macromolecules, Vol. 20, Issue 11, p. 2949-2951 https://doi.org/10.1021/ma00177a053	journal	November 1987
Polymerization of Enantiomerically Pure 2,3-Dicarboalkoxynorbornadienes and 5,6-Disubstituted Norbornenes by Well-Characterized Molybdenum Ring-Opening Metathesis Polymerization Initiators. Direct Determination of Tacticity in Cis, Highly Tactic and Trans, Highly Tactic Polymers O'Dell, Richard; McConville, David H.; Hofmeister, Gretchen E. Journal of the American Chemical Society, Vol. 116, Issue 8, p. 3414-3423 https://doi.org/10.1021/ja00087a028	journal	April 1994
Ring-opening Polymerization of Norbornene and Its Derivatives by MoCl₅, WCl₆ and ReCl₅ Catalysts Oshika, Takao; Tabuchi, Hiroyoshi Bulletin of the Chemical Society of Japan, Vol. 41, Issue 1, p. 211-217 https://doi.org/10.1246/bcsj.41.211	journal	January 1968
Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes Peryshkov, Dmitry V.; Schrock, Richard R.; Takase, Michael K. Journal of the American Chemical Society, Vol. 133, Issue 51, p. 20754-20757 https://doi.org/10.1021/ja210349m	journal	December 2011
Exploring Factors That Determine Cis/Trans Structure and Tacticity in Polymers Prepared by Ring-Opening Metathesis Polymerizations with Initiators of the Type syn- and anti-Mo(NAr)(CHCMe₂Ph)(OR)₂. Observation of a Temperature-Dependent Cis/Trans Ratio Schrock, Richard R.; Lee, Jin-Kyu; O'Dell, Richard Macromolecules, Vol. 28, Issue 17, p. 5933-5940 https://doi.org/10.1021/ma00121a033	journal	August 1995
Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts Schrock, Richard R.; Hoveyda, Amir H. Angewandte Chemie International Edition, Vol. 42, Issue 38, p. 4592-4633 https://doi.org/10.1002/anie.200300576	journal	October 2003
Synthesis of stereoregular ROMP polymers using molybdenum and tungsten imido alkylidene initiators Schrock, Richard R. Dalton Transactions, Vol. 40, Issue 29, p. 7484-7495 https://doi.org/10.1039/c1dt10215j	journal	May 2011
Synthesis of Tungsten Oxo Alkylidene Complexes Peryshkov, Dmitry V.; Schrock, Richard R. Organometallics, Vol. 31, Issue 20, p. 7278-7286 https://doi.org/10.1021/om3008579	journal	October 2012
Synthesis and ROMP Chemistry of Decafluoroterphenoxide Molybdenum Imido Alkylidene and Ethylene Complexes Yuan, Jian; Schrock, Richard R.; Gerber, Laura C. H. Organometallics, Vol. 32, Issue 10, p. 2983-2992 https://doi.org/10.1021/om400199u	journal	May 2013
¹³C N.m.r. Spectra of ring-opened polymers of 1-methylbicyclo[2.2.1]hept-2-ene and their hydrogenated products Hamilton, James G.; Ivin, Kenneth J.; Rooney, John J. British Polymer Journal, Vol. 16, Issue 1, p. 21-33 https://doi.org/10.1002/pi.4980160106	journal	March 1984
B(C₆F₅)₃ Activation of Oxo Tungsten Complexes That Are Relevant to Olefin Metathesis Peryshkov, Dmitry V.; Forrest, William P.; Schrock, Richard R. Organometallics, Vol. 32, Issue 19, p. 5256-5259 https://doi.org/10.1021/om4007906	journal	September 2013
Linear polymerization of endo‐dicyclopentadiene initiated by metathesis catalysts Pacreau, Annie; Fontanille, Michel Die Makromolekulare Chemie, Vol. 188, Issue 11, p. 2585-2595 https://doi.org/10.1002/macp.1987.021881110	journal	November 1987

Similar Records

Catalysts and methods for ring opening metathesis polymerization

Patent · Tue Apr 04 00:00:00 EDT 2017 · OSTI ID:1433368

Schrock, Richard Royce; Autenrieth, Benjamin

Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo -Dicyclopentadiene by Molybdenum and Tungsten Catalysts

Journal Article · Fri Apr 17 00:00:00 EDT 2015 · Macromolecules · OSTI ID:1433368

Autenrieth, Benjamin; Jeong, Hyangsoo; Forrest, William P.; +5 more

Metathesis catalysts and methods thereof

Patent · Tue Apr 19 00:00:00 EDT 2016 · OSTI ID:1433368

Schrock, Richard Royce; Yuan, Jian

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Catalysts and methods for ring opening metathesis polymerization

Citation Formats

References (33)

Similar Records

Related Subjects